Theodor diehl



UNITED STATES PATENT ()FFICE.

THEODOR DIEHL, or MANNHEIM, BADEN, GERMANY, ASSIGNOR TO enone CARL ZIMMER, OF SAME PLACE.

COLORING-MATTER FROM THE SULPHO-ACIDS 0F ETH YL 0R DIPHENYLAMINE COMBINED wml TETRAZO- DIPHENYL 0R TETRAZODITQLYL. I

SPECIFICATION forming part of Letters Patent No. 380,098, dated March 27, 1888.

Application filed November 29, 1887.

To all whom it may concern:

Be it known thatI, Doctor THEODOR DIEHL, a subject of the Emperor of Germany, resident at Mannheim, Germany, (assignor to the firm of GEORG CARL ZIMMER, of Mannheim,) have invented new and useful Improvements in C01- oring-Matters, of which the following is aspecification.

I have discovered that the sulpho-acids obtained from monoethylanilin or diphenylamine can, by the processes hereinafter described, be combined with tetrazodiphenyl or tetrazoditolyl to produce new coloring-matters that dye cotton in the soap bath, and which are partly remarkable for their fiery tints and their comparatively permanent nature.

The following may serve as examples of the production of coloring-matters according to this invention:

pound formed is poured under continual stirring into a solution of forty-six kilos monoethylanilin-sulphonate of soda in six hundred liters of water, to which is added so much ace tate of soda that all mineral acid is bound.

After about twelve hours stirring the reaction will be complete, the separated color-acid is converted into its soda salt, and this is salted out. The coloring-matter,which dissolves with difficulty. dyes cotton a sulphur yellow.

2. Benzidt'n two molecules of diphenylamincsuZpho-acid.-The monoethylanilinsulphoacid of the previous example is replaced by fifty-- four kilos diphenylamine-monosulphonate of soda, producing a coloring-matter that dyes cotton reddish yellow.

3. Benzidin d'iphenylaminesulpho acid ethyZaniZ insaZpho-acidr-282 kilos benzidin-sulphate are diazotized as described, the solution of the tetrazo compound is poured under stirring into twenty-seven kilos diphenylaminesulphonate of soda, and thirty-five kilos acetate phenol.-28.2 kilos benzidin phonate of soda.

Serial No. 256.422. (No specimens.)

of soda dissolved insix hundred liters of water. Theblackish-brown intermediate product formed is introduced into a solution of twenty.- three kilos monoethylanilin-sulphonate of soda and six kilos carbonate of soda in about nine hundred liters water. After stirring for twelve hours, the color solution is boiled and filtered, and the coloring-matter is then salted out. It dissolves with some difficulty, the same as Nos. 1 and 2, and dyes cotton a reddish yellow.

B. 1. Bcnzidz'n diphenylamincsalpho acid I are diazotized, as in the previous examples, and combined with twenty-seven kilos diphenylamine-sul-v The formed intermediate compound is added to an alkaline solution of 9.5 kilos phenol in aboutsix hundred liters water. The solution is stirred again for about twelve hours, is then boiled and filtered,and

' the coloring-matter issalted out. This produces a yellow tint on cotton.

2. Benzidm dtphenylaminesalpho acid cres0Z.-If in the foregoing example the phenol is replaced by eleven kilos cresol, a coloring.

matter is produced that dyes somewhat morered than the preceding one.

3. Benzidin dtphcnylaminesulpho acid and resorcin.If in place of the phenol in example 1 eleven kilos resorcin are used under other wise the same conditions, a coloring-matter is produced that dyes cotton in the soap bath with an orange-red color.

4. Bcnzidin diphcnylaminesalpho acid salicylic acid-By combining the above-described intermediate product with sixteen kilos salicylic acid an orange-yellow product will be obtained. 7

5. Bcnzidvln cthylam'linszdpho acid I naphthz'om'c acid-The tetrazo compound produced from 28.2 kilos benzidin sulphate can be combined withtwenty-three kilos monoethylanilinsulphonat-e of soda under the same conditions as described in example No. 1. The orangecolored intermediate product then acts upon twenty-six kilos naphthionate with formation of a red coloring-matter thatis considerably yellower than the dye known as Congo red.

6. Benzidin d'iphenylamincsulpho acid naphthz'onia acid.-The intermediate product from benzidin and diphenylaminesulpho-acid, already described, combines in an analogous manner with twenty-six kilos naphthionate to form a red coloring-matter,which in suit stands between that above mentioned and Congo red.

7. Tolidin-l-dqihenylaminesuqaho-acid naphthiom'c acid.--In the preparation of tetrazoditolyl Iproceed as in the preparation of tetrazodiphenyl, only with the difference that 31.2 kilos tolidin sulphate are used. The intermediate product produced with twenty-seven kilos diphenylaminesulpho-acid reacts upon twentysix kilos naphthionate with formation of a bluish -red coloring-matter. v

8. Benzidz'n l diphenylaminesulpho acid betanaphtholsulpho-acid.-Iftheabove-described intermediate prod not is combined with twentysix kilos betanaphtholmonosulphonate of soda (Schafl'er) in alkaline solution; a violet-red coloring-matter is produced.

9. Toh'din+diphenylaminesuqiho a0id+alpka-, naphtholalphasulpho-acid.1f the intermediate product obtained from tolidin diphenylaminesulpho-acid is made to react upon alphanaphtholalphamonosulpho acid, a red violet coloring-matter is produced.

10. Benzidin diphenylaminesulpho acid betanaphiholdisulpho acid.If, instead of the betanaphtholmonosulpho acids in examples Sand 9, the equivalent quantities ofadisulphoacid are used, reddish-violet coloring-matters are formed.

Having thus described myinvention and the manner of employing the same, what I claim as my invention, and wish to have secured to me by Letters Patent of the United States of America, is

1. The production of coloring-matters that dye unmordanted cotton directly by the action of one molecule of tetrazo salt upon two molecules of the sulpho-acids of monoethylanilin or diphenylamine.

2. The production of coloring-matters that dye unmordanted cotton directly by the action of one molecule of the sulpho-acids referred to in theprecedingclaim,and thesubsequentcombination with phenols, salicylic acids, phenolsulpho-acids, the sulpho-acids of alpha and beta naphthol or of alpha and beta naphthyla mine.

In testimony whereof I have signed my name to this specification in the presence of two subscribing witnesses.

THEODOR DIEHL.

Witnesses:

J. F. MONAGHAN, H. E. HAMMOND. 

